Currently finalizing a deal for another property with a different individual investor where we will have the same payout model, but they will put up a bit more cash to cover all the admin work I have to do to set things up. 

During your initial walkthrough, inspect the property for any major issues such as structural damage, roofing problems, plumbing, and electrical concerns, while documenting all cosmetic and functional issues with detailed photos and notes.Once you confirm the property’s potential, finalize your ARV and calculate the repair costs using either a reliable estimator or insights from contractors.

Also the value (in this case) is determined by the NOI, so assuming it will be worth 2x, is assuming your NOI is thru the roof (which is can be, but it's not likely in the first 5 years).

So to help cover expenses and see some cash flow would focus on multi-unit property. 

Use a reputable expert like @Dave Foster and you’ll be covered.

Are you trying to afford a house much more expensive than your W2s could cover? 

One thing I'm trying to do is to test different cover photos to see which ones draw a greater % of click-thrus (which seems like a reasonable thing to test).I'd like to be able to view the Airbnb stats to see, for each cover photo I test, things like what % of people click through on it.

Mainly I’m trying to avoid “aged poorly design” glassblock walls, small bedrooms, older windows (wood/aluminum, single pane), aluminum patio covers, and to a lesser extent landscaping.

Hi Owen- Most others have covered the specific areas to consider.

I am also of the belief that if a property cannot produce $1500-2000+ in rent per month, you're just going to have a hard time covering capex.